HCID 67155628, compound → HCID 44481362, compound

Participants

Reaction Steps

(+)-N-benzyl-N-methyl-1-[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methanamine (0.37 g, 1.06 mmol), palladium on carbon (10%, 45 mg) and EtOH (20 ml) was hydrogenated at 45 psi for 14 h. Purification by flash chromatography (EtOAc/MeOH 2:1) afforded the pure title compound (0.24 g, 89%, >95% e.e.). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 224° C. [α]DMeOH=+77°. 1H-NMR (400 MHz, MeOH): δ 7.48 (1h, dd, J1 8.0 Hz, J2 1.6 Hz), δ 7.43 (1H, d, J 2.0 Hz), δ 7.18 (1H, d, J 8.0 Hz), δ 5.19 (1H, t, J 4.8 Hz), δ 5.00 (2H, dd, J 50 Hz, J2 16 Hz), δ 3.03 (3H, s), δ 2.99 (2H, d, J 4.0 Hz), δ 2.53 (3H, s), δ 1.54 (1H, s).

Provenance & Evidence